Modern advertising and solicitation campaigns involve the assembly and mailing of hundreds of thousands of envelopes each containing a plurality of letters of appeal, coupons, order blanks, return envelopes, leaflets offering services and/or products and the like, and very often inexpensively-produced ball-point pens. Machines have been made which move numbers of envelopes past inserting stations where the various items are inserted into each envelope as it passes each station. The construction of the basic machine is such that the envelope is held open as it passes down the line of insert stations. When the inserts are generally flat, each insert is moved into the open envelope by a reciprocating finger or vacuum device moving over the stack of the insert. Insertion of objects such as the ball-point pens does not lend itself to such a manner of insertion. Manual insertion of a pen is feasible but slow and controls the ultimate speed at which the insertion process can be maintained. Currently, insertion machines process envelopes up to a rate of 3,000 envelopes per hour. Machines to insert pens have been developed but have not been capable of operating at the speed of 3,000 inserts of pens per hour. The insertion rate has been less than 500 per hour and the insertions have been halted by feeding jams and mechanical failures of the machines.